Distributed electric propulsion (DEP) concepts leverage the synergistic benefits of aeropropulsive coupling and improve the overall flight efficiency by placing propulsors at optimal locations, such as the wingtip. However, placing propulsors far away from the aircraft centerline may bring aircraft difficulties in complying with critical-engine-inoperative flight certification rules. To investigate the impact of certification requirements on the DEP aircraft design, this paper takes NASA’s PEGASUS concept as a use case and presents a study of certification-constrained vertical tail sizing and propulsive power split optimization. For comparison, a vertical tail retrofit study is also conducted on the ATR 42-500 aircraft using the same design space, to gain insights into the different impacts of certification constraints on the design process between conventional and unconventional aircraft. In each study, a design space exploration is performed, including a feasibility test and a multi-objective optimization. The feasibility test shows that the certification constraints yield a much smaller feasible design space for the DEP concept when compared to the conventional aircraft. Despite a much smaller feasible design space, the constrained Pareto optima of the PEGASUS still exhibit lower cruise drag coefficient, fuel burn, and operational energy cost when compared to those of the ATR 42.